1,287
Views
12
CrossRef citations to date
0
Altmetric
Research Article

Through scaffold modification to 3,5-diaryl-4,5-dihydroisoxazoles: new potent and selective inhibitors of monoamine oxidase B

, , , , , , , , , , & show all
Pages 264-270 | Received 04 Aug 2016, Accepted 05 Sep 2016, Published online: 18 Jan 2017

References

  • Singer TP, Von Korff RW, Murphy DL, eds. Monoamine oxidase: structure, function, and altered functions. [Papers from a Symposium Held at the Michigan Molecular Institute, Midland, on July 15–19, 1979]. Academic Press; 1979:557 pp.
  • Mure M, Mills SA, Klinman JP. Catalytic mechanism of the Topa quinone containing copper amine oxidases. Biochemistry 2002;41:9269–78.
  • Kumar B, Sheetal Mantha AK, Kumar V. Recent developments on the structure–activity relationship studies of MAO inhibitors and their role in different neurological disorders. RSC Adv 2016;6:42660–83.
  • Naoi M, Maruyama W, Inaba-Hasegawa K. Type A and B monoamine oxidase in age-related neurodegenerative disorders: their distinct roles in neuronal death and survival. Curr Top Med Chem (Sharjah, United Arab Emirates) 2012;12:2177–88.
  • Shih JC, Chen K, Ridd MJ. Monoamine oxidase: from genes to behavior. Annu Rev Neurosci 1999;22:197–217.
  • Kong P, Zhang B, Lei P, et al. Neuroprotection of MAO-B inhibitor and dopamine agonist in Parkinson disease. Int J Clin Exp Med 2015;8:431–9.
  • Jha SK, Jha NK, Kumar D, et al. Linking mitochondrial dysfunction, metabolic syndrome and stress signaling in neurodegeneration. Biochim Biophys Acta Mol Basis Dis 2016 [Epub ahead of print]. DOI: 10.1016/j.bbadis.2016.06.015.
  • Giladi N, Asgharnejad M, Bauer L, et al. Rotigotine in combination with the MAO-B inhibitor selegiline in early Parkinson's disease: a post hoc analysis. J Parkinsons Dis 2016;6:401–11.
  • Perez-Lloret S, Rascol O. The safety and efficacy of safinamide mesylate for the treatment of Parkinson's disease. Expert Rev Neurother 2016;16:245–58.
  • Wang Y, Sun Y, Guo Y, et al. Dual functional cholinesterase and MAO inhibitors for the treatment of Alzheimer's disease: synthesis, pharmacological analysis and molecular modeling of homoisoflavonoid derivatives. J Enzyme Inhib Med Chem 2016;31:389–97.
  • Chimenti F, Maccioni E, Secci D, et al. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazole derivatives. J Med Chem 2005;48:7113–22.
  • Cardia MC, Sanna ML, Meleddu R, et al. A novel series of 3,4-disubstituted dihydropyrazoles. Synthesis and evaluation for MAO enzyme inhibition. J Heterocycl Chem 2013;50:E87–92.
  • Secci D, Carradori S, Bolasco A, et al. Discovery and optimization of pyrazoline derivatives as promising monoamine oxidase inhibitors. Curr Top Med Chem (Sharjah, United Arab Emirates) 2012;12:2240–57.
  • Maccioni E, Alcaro S, Orallo F, et al. Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase. Eur J Med Chem 2010;45:4490–8.
  • Carradori S, Silvestri R. New frontiers in selective human MAO-B inhibitors. J Med Chem 2015;58:6717–32.
  • Chimenti F, Maccioni E, Secci D, et al. Selective inhibitory activity against MAO and molecular modeling studies of 2-thiazolylhydrazone derivatives. J Med Chem 2007;50:707–12.
  • Chimenti F, Maccioni E, Secci D, et al. Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones. J Med Chem 2008;51:4874–80.
  • Chimenti F, Secci D, Bolasco A, et al. Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors. Bioorg Med Chem 2010;18:5063–70.
  • Distinto S, Yanez M, Alcaro S, et al. Synthesis and biological assessment of novel 2-thiazolylhydrazones and computational analysis of their recognition by monoamine oxidase B. Eur J Med Chem 2012;48:284–95.
  • Maccioni E, Alcaro S, Cirilli R, et al. 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles: a new scaffold for the selective inhibition of monoamine oxidase B. J Med Chem 2011;54:6394–8.
  • Distinto S, Meleddu R, Yanez M, et al. Drug design, synthesis, in vitro and in silico evaluation of selective monoaminoxidase B inhibitors based on 3-acetyl-2-dichlorophenyl-5-aryl-2,3-dihydro-1,3,4-oxadiazole chemical scaffold. Eur J Med Chem 2016;108:542–52.
  • Cerioni G, Maccioni E, Cardia MC, et al. Characterization of 2,5-diaryl-1,3,4-oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very remote Hammett correlation. Magn Reson Chem 2009;47:727–33.
  • Sanna ML, Maccioni E, Vigo S, et al. Application of an immobilised amylose-based chiral stationary phase to the development of new monoamine oxidase B inhibitors. Talanta 2010;82:426–31.
  • Cer RZ, Mudunuri U, Stephens R, Lebeda FJ. IC50-to-Ki: a web-based tool for converting IC50 to Ki values for inhibitors of enzyme activity and ligand binding. Nucleic Acids Res 2009;37:W441–5.
  • Binda C, Wang J, Pisani L, et al. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs. J Med Chem 2007;50:5848–52.
  • Berman HM, Westbrook J, Feng Z, et al. The Protein Data Bank. Nucleic Acids Res 2000;28:235–42.
  • Schrödinger LLC. Maestro GUI. New York (NY); 2015.
  • Mohamadi F, Richards NGJ, Guida WC, et al. Macromodel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J Comput Chem 1990;11:440–67.
  • Halgren T. Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J Comput Chem 1996;17:520–52.
  • Still WC, Tempczyk A, Hawley RC, Hendrickson T. Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 1990;112:6127–9.
  • Schrödinger LLC. QMPolarized protocol. Schrodinger Suite. New York (NY); 2015.
  • McDonald DQ, Still WC. AMBER torsional parameters for the peptide backbone. Tetrahedron Lett 1992;33:7743–6.
  • Kollman PA, Massova I, Reyes C, et al. Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models. Acc Chem Res 2000;33:889–97.
  • PyMOL. Version 1.5.0.4. Molecular Graphics System. Schrödinger, LLC.
  • He X-f, Lan Y, Zhang Q, et al. Deferoxamine inhibits microglial activation, attenuates blood-brain barrier disruption, rescues dendritic damage, and improves spatial memory in a mouse model of microhemorrhages. J Neurochem 2016;138:436–47.
  • Dexter DT, Statton SA, Whitmore C, et al. Clinically available iron chelators induce neuroprotection in the 6-OHDA model of Parkinson's disease after peripheral administration. J Neural Transm (Vienna) 2011;118:223–31.
  • Santos MA, Chand K, Chaves S. Recent progress in multifunctional metal chelators as potential drugs for Alzheimer's disease. Coord Chem Rev 2016;327–328:287–303.
  • Meleddu R, Distinto S, Corona A, et al. Exploring the thiazole scaffold for the identification of new agents for the treatment of fluconazole resistant Candida. J Enzym Inhibit Med Chem 2016;31:1672–7.
  • Cho AE, Guallar V, Berne BJ, Friesner R. Importance of accurate charges in molecular docking: quantum mechanical/molecular mechanical (QM/MM) approach. J Comput Chem 2005;26:915–31.
  • Chung JY, Hah J-M, Cho AE. Correlation between performance of QM/MM docking and simple classification of binding sites. J Chem Inform Model 2009;49:2382–7.
  • Binda C, Li M, Hubálek F, et al. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures. Proc Natl Acad Sci USA 2003;100:9750–5.
  • Edmondson DE, Binda C, Mattevi A. Structural insights into the mechanism of amine oxidation by monoamine oxidases A and B. Arch Biochem Biophys 2007;464:269–76.
  • Cattaneo C, Sardina M, Bonizzoni E. Safinamide as add-on therapy to levodopa in mid- to late-stage Parkinson's disease fluctuating patients: post hoc analyses of studies 016 and SETTLE. J Parkinsons Dis 2016;6:165–73.